Synthesis of arylselenide ethers by photoinduced reactions of selenobenzamide, selenourea and selenocyanate anions with aryl halides

TETRAHEDRON LETTERS

卷:52

Article

Bouchet, Lydia M.¹  Penenory, Alicia B.¹  Argueello, Juan E.¹ 

[1] Univ Nacl Cordoba, Fac Ciencias Quim, Dept Quim Organ, INFIQC, RA-5000 Cordoba, Argentina

关键词: Selenides;    S(RN)1;    Photochemistry;    Electron transfer;    Radical;   

DOI  :  10.1016/j.tetlet.2010.11.115

来源: Elsevier

【 摘 要 】

Selenobenzamide (-SeCNH(Ph), 1), selenourea (-SeCNH(NH2), 2) and selenocyanate (-SeCN, 3) anions afford areneselenolate ions (ArSe-) under photostimulation in the presence of tert-butoxide or 2-naphthoxide ions as electron donors (entrainment conditions) in DMSO. In a 'one-pot' procedure, ArSe- anions can be trapped by a subsequent aliphatic nucleophilic substitution giving aryl methyl selenides in good to excellent yields (67-100%). This simple approach is compatible with electron-donating and electron-withdrawing substituents, such as nitro and carbonyl groups. (C) 2010 Elsevier Ltd. All rights reserved.

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